| Winona to Olympia (Washington) | 1,514.86 mi (2,437.92 km) |
| Winona to Olympia Heights (Florida) | 1,416.52 mi (2,279.67 km) |
| Winona to Omaha (Nebraska) | 294.43 mi (473.85 km) |
| Winona to On Top of the World Designated Place (Florida) | 1,154.51 mi (1,858.00 km) |
| Winona to Onalaska (Wisconsin) | 25.51 mi (41.06 km) |
| Winona to Oneida (New York) | 802.91 mi (1,292.15 km) |
| Winona to Oneonta (New York) | 841.23 mi (1,353.83 km) |
| Winona to Ontario (California) | 1,545.26 mi (2,486.85 km) |
| Winona to Ontario (Oregon) | 1,252.04 mi (2,014.96 km) |
| Winona to Opa-locka (Florida) | 1,407.54 mi (2,265.22 km) |
| Winona to Opelika (Alabama) | 856.91 mi (1,379.07 km) |
| Winona to Opelousas (Louisiana) | 934.78 mi (1,504.38 km) |
| Winona to Orange (California) | 1,564.65 mi (2,518.05 km) |
| Winona to Orange (Texas) | 969.12 mi (1,559.64 km) |
| Winona to Orange City (Florida) | 1,190.70 mi (1,916.25 km) |
